


Step into My Office

by Wayward04



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Established Dean Winchester/Sam Winchester, M/M, Top Dean Winchester/Bottom Sam Winchester
Language: English
Status: Completed
Published: 2019-09-19
Updated: 2019-09-19
Packaged: 2020-10-21 16:21:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,829
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20696468
Author URL: https://archiveofourown.org/users/Wayward04/pseuds/Wayward04
Summary: Set during the episode After School Special (4x13). Just something that happened after they turned the cameras off. ;)





	Step into My Office

Sam watched his brother with amusement from behind the door to the gym as Dean lectured the class on the finer points of dodgeball. The older Winchester was wearing the most ridiculous outfit. There was a red sweatband keeping his short hair off of his forehead, a white t-shirt, red shorts that looked like they came straight from Magnum PI’s closet, white tube socks, and white gym shoes. Dean started walking back and forth along the line of students as he continued speaking and suddenly Sam decided that the shorts, at least, may not be so bad after all. The fabric outlined almost scandalously his brother’s extremely well formed ass in the back and the bulge of his cock in the front. Sam swallowed hard as he watched the muscles in Dean’s thighs flex as he walked. The younger Winchester’s dick twitched as he imagined the way those same thighs moved as his brother fucked him hard.  
Dean looked up and noticed Sam standing there, making him jump slightly. The younger man gestured with his head, and the older told the kids to go nuts, tossing a bag of red balls toward them. Dean joined Sam at the door.  
“What’s up?” the older Winchester asked.  
Sam filled Dean in on what he had learned regarding the case. Then he smirked and ran his eyes down his brother’s body. “Nice shorts.”  
The older man’s eyes lit up. “Yeah? They’re pretty awesome, right?” Dean put his hands on his hips and posed dramatically.  
The younger snorted. “Actually the 80’s called and they need them back immediately, but they’re not completely without their charms.” Sam craned his neck to get another view of his brother’s ass. “What are you doing for lunch?”  
Dean bit his bottom lip and his eyes crinkled at the corners. “Well, it’s sloppy joes day in the cafeteria but other than that I got nothing going. You thinking you might want some of this?”  
Sam pressed his lips together to keep from laughing. He gestured to his janitor’s coveralls. “I’ve got a real shitty office if you want to meet there after you pig out on your sloppy joes.”  
The older man winked. “It’s a date,” he said, going back to his class.  
A couple hours later, Sam was in the janitor’s closet/office trying to do some research on his laptop when the door cracked open and Dean slipped in, locking the door behind him.   
“Finding anything?” he asked, nodding towards the computer.  
“Not yet,” Sam responded, pushing up from his chair.  
Dean looked around the office. It actually wasn’t too bad. It hadn’t changed in the 10 years since they had attended there, it was dirty, and it smelled like too many cleaning supplies in one place, but it was a pretty good size for what it was. It held the metal desk and chair and several metal shelving units that held all the supplies and tools a janitor could need.  
“This closet looks familiar,” Dean said, a gleam in his eye, “Did I fuck you in here when we went to this school?”  
Sam’s faced burned. He had forgotten about that. The janitor rarely ever went into his office except to restock his cart or eat his lunch so young Sam and Dean had snuck in here for a fast fuck whenever the older Winchester could convince his little brother to miss a few minutes of a class or during lunch.  
“Yeah,” he mumbled, “Quite a few times, actually.”  
Dean grinned. “I knew it! Man, you were sexy back then. That tight little ass and tiny teenager dick. You used to squeal so pretty for me when I would fuck you good and hard.” He whistled appreciatively at the memory.  
Sam’s mouth dropped open. “What?” he rasped, trying not to yell, “I didn’t have a tiny dick and I didn’t squeal!”  
The older man’s eyes darted down to the younger’s now fully grown member. “Fine, it wasn’t tiny but it sure wasn’t what it is now.” Dean stalked slowly toward his brother, pushing Sam against the desk. The metal scraped along the concrete floor as the older Winchester ran his hands up the younger’s thighs and grabbed his ass. “And you know you make all kinds of sounds when I’m fucking you. I bet I could make you squeal right now if I wanted to.”  
Sam looked into Dean’s green eyes as if he were hypnotized and without meaning to, made a whimpering sound. At his brother’s satisfied smirk, the younger man quickly cleared his throat to hide his previous slightly-less-than-manly tone. Dean leaned forward slowly and kissed Sam.   
The kiss was soft at first. The older man brought one hand up to the younger’s jaw, the other digging into Sam’s hip. Sam opened his mouth and licked at Dean’s lips. The older Winchester smiled and opened up for his brother, welcoming Sam’s tongue into his mouth. Both men moaned at the connection and Dean suddenly took both hands and grabbed his little brother’s ass. He pressed their erections together and began kissing Sam more insistently. Dean took over complete control of the kiss and tangled their tongues together, wanting to taste every inch of Sam’s tongue and lips. The younger man roughly pulled up the older’s t-shirt, pushing his hands underneath to run his fingers up his brother’s back. He whimpered again, not caring anymore about the sounds he made.  
Without breaking the kiss, Dean reached for the zipper of Sam’s coveralls, and the younger man stood to give his brother better access. The older Winchester pulled the zipper down all the way and pushed the garment down Sam’s shoulders. Dean pushed away in frustration.  
“Shit, Sammy, how many layers are you wearing?” he complained.   
Sam was wearing his regular flannel, undershirt, and jeans underneath the coveralls. The younger man frowned. “Coveralls aren’t like a romper or whatever. I wouldn’t be naked underneath.”  
Dean ignored Sam as he helped him take off the uniform and continued grumbling. “Like a damn bride on her wedding night.” The younger man laughed. Dean pointed at the metal shelving. “Okay, princess, hands on the shelf over there.”  
Sam quickly moved to obey, placing his hands next to extra rolls of toilet paper and sticking his ass out. The older man came up behind him and moaned appreciatively, running his hands along his brother’s body.  
“So pretty like this, baby boy,” Dean said softly.  
The older man reached up with one hand and moved the younger’s hair off his neck and began kissing along the skin there, his other hand undoing Sam’s belt. Sam moaned and whimpered, already painfully hard in anticipation. Dean then took both hands and slowly pushed Sam’s pants down to his knees.   
“Shit. We don’t have any lube,” the older man realized. He stared dubiously at the items on the shelves.  
“I have some in my pocket,” the younger panted.  
Dean grinned. “Regular little boy scout, aren’t you, baby?” He fished the small bottle out of the pocket of Sam’s jeans and poured a generous amount on two fingers.  
The older man swirled his fingers around the younger’s hole and gently pushed through the first ring of muscle. Sam moaned as Dean’s fingers entered his channel and began moving slowly in and out.  
“De, that feel so good.”  
Dean smiled and rubbed one of Sam’s shoulders as he continued moving his fingers in and out of his brother’s body, scissoring them as he went. When the younger man’s passage felt loose enough, the older removed his fingers and pushed his shorts past his ass. Dean lubed up his cock and lined it up with Sam’s entrance. He grabbed one of his little brother’s hips and with the other hand guided his dick slowly inside.  
“Ah, fuck,” Sam moaned, “Fuck, more, faster!”  
“Shh, I got you, baby boy.” Dean continued gently pushing inside his brother’s channel until he was fully sheathed. He paused for a minute, allowing Sam to adjust to the intrusion, placing kisses along the younger man’s back.  
“Ah, De, move, I need you.”  
Dean frowned. “Stop it, now, I don’t want to hurt you.” He moved his hips back slowly and pushed back in. “Why are you being so needy right now?”  
Sam began moaning softly as the older man kept up his steady pace. “Your shorts are ridiculous but you looked so sexy in them earlier and I wanted you so bad.”   
The older man chuckled. “Okay, baby boy, you got me. I’ll take care of you.”  
Dean put his hands on Sam’s hips. He leaned his pelvis back almost to the point of pulling out then thrust back in hard. The younger man let out a strangled cry. The older’s dick felt so good, but Sam knew there could potentially be dozens of kids on the other side of the wall and he didn’t want to blow their cover by being too loud. Dean began pounding Sam’s ass hard and fast. The younger man grunted with each thrust, screwing his eyes shut and gripping the cold metal of the shelving with white-knuckled fists. Sam could feel his orgasm building in his belly as Dean hit his prostate over and over.   
“Fuck, De! I’m gonna come!”   
The older man took the younger’s cock in one hand and began stroking it. “I got you, Sammy. Give it to me, baby.” Dean pressed a kiss on the back of his brother’s neck.   
Sam growled as he shot thick white ropes over Dean’s hand and who knew what else. Stars burst behind his eyelids and he focused on his breathing so that he wouldn’t pass out. Sam’s channel clenched around his brother’s dick and Dean’s fingers on his hip dug into his flesh, making him think he’d have marks later. The older man cursed and said the younger’s name in a broken whisper as he also climaxed.   
When they had both come back to earth, Dean slowly pulled out of his brother’s body. Sam whimpered at the loss and groaned as he stood upright, stretching his sore muscles. Dean found a cloth from a box of brand-new rags and cleaned them up. They got themselves back together and the older man wrapped his arms around his brother.  
Dean pecked Sam on the lips. “Sorry you don’t like my outfit,” he joked.  
The younger man gave a satisfied smile. “It’s starting to grow on me.”  
Dean kissed Sam again and pulled away. “Well, I could stand here and kiss you all day, but we should get back to the case. Let me know if anything else happens.”  
Sam sighed and wrinkled his nose. “Yep, I will.”  
The older man flipped the lock and opened the door. Before he slipped back out into the hallway, Dean turned his head and winked. “Sammy. That was fun.”  
Sam smiled as his brother closed the door behind him. He pulled his coveralls back on and walked back to his desk.


End file.
